Potassium Nitrate → 7-Fluoro-6-nitro-5-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedione

HRID 53779Notes

Reaction equation

HRID 53779 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9]2)=[C:4]([C:14]([F:17])([F:16])[F:15])[CH:3]=1.[N+:18]([O-])([O-:20])=[O:19].[K+]>OS(O)(=O)=O.[OH-].[K+]>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9]2)=[C:4]([C:14]([F:16])([F:17])[F:15])[C:3]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 2

HCID 24434Potassium NitrateHCID 106105237-Fluoro-5-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedione

Product 1

HCID 211899657-Fluoro-6-nitro-5-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedioneYield 76.8%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 14797Potassium HydroxideSolvent

Procedure

To a solution of 7-fluoro-5-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedione (60 mg, 0.24 mmol) in concentrated H2SO4 (1 mL) at 0° C. was added KNO3 (27 mg, 0.26 mmol, Baker). The mixture was stirred at 90°-100° C. for 14 h, then cooled to room temperature and poured into ice water (2 g). The precipitate was collected by filtration, affording 64 mg (90%) of crude title compound. It was dissolved in 1N KOH (2 mL) and filtered. The filtrate was acidified to pH=2 with 4N HCl to give a yellow precipitate, which was collected by filtration, then was dried in the air at 50° C. for 4 h, affording pure title compound (54 mg, 76%) as a yellow powder. Mp: 305°-307° C.; IR (KBr, cm-1): 3418, 3124, 2971, 1717, 1624, 1556; 1H NMR (DMSO-d6): δ 7.422 (d, 1H, J=10.2 Hz), 11.765 (br, 1H), 12.532 (s, 1H). HRMS: calcd for C9H3F4N3O4 (M+) m/z: 293.0086, found: 293.0071.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customaffording 64 mg (90%) of crude title compound
  3. filtrationfiltered
  4. customto give a yellow precipitate, which
  5. filtrationwas collected by filtration
  6. customwas dried in the air at 50° C. for 4 h

Sources & evidence

ORD record
ord-44ce84b57f084afc80bd271a151b3b89
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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